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Nitromethane → (2,6-difluoro-3-nitro-phenyl)-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone

HRID 217590
Notes
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Reaction equation

HRID 217590 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[Cl-].[Cl-].[Cl-].[Al+3].[N+](C)([O-])=O.[F:19][C:20]1[C:28]([N+:29]([O-:31])=[O:30])=[CH:27][CH:26]=[C:25]([F:32])[C:21]=1[C:22](Cl)=[O:23]>C(OCC)(=O)C.O.Cl.CO>[F:19][C:20]1[C:28]([N+:29]([O-:31])=[O:30])=[CH:27][CH:26]=[C:25]([F:32])[C:21]=1[C:22]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)[NH:8][CH:9]=1)=[O:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 6375NitromethaneHCID 27817562,6-Difluoro-3-nitrobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 205974295-methyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 59569621(2,6-difluoro-3-nitro-phenyl)-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanoneYield 60%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 5-methyl-1H-pyrrolo[2,3-b]pyridine (15, 2.00 g, 15.1 mmol) and aluminum trichloride (11.6 g, 87.2 mmol), nitromethane (63.1 mL, 1.16 mol) was added, followed by the addition of 2,6-difluoro-3-nitro-benzoyl chloride (14, 3.22 g, 14.5 mmol). The reaction was placed in an oil bath at 45° C. and stirred for 3 days, then cooled to room temperature and 30 mL of methanol was added. The reaction was then diluted with 200 mL of ethyl acetate and 100 mL each of water and 1N hydrochloric acid, resulting in a precipitate that was collected to provide the desired compound (16, 2.761 g). Additional compound was recovered from the organic layer, removing the solvent and purifying by silica gel column chromatography eluting with a gradient of 5 to 70% ethyl acetate in hexanes to provide another 126 mg of compound. MS (ESI) [M+H+]+=317.9.

Workup

  1. customThe reaction was placed in an oil bath at 45° C.
  2. customresulting in a precipitate that
  3. customwas collected

Sources & evidence

ORD record
ord-33b9b6deafb44137b00bbefe0760f7a9
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08198273B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes